Modern organizations are often required to enter into complex or expansive contracts between each other, vendors, suppliers, clients, or the like. In some cases, complex contracts may require a significant amount of effort to establish between parties. This effort may include common activities, such as, term negotiating, back-and-forth review, local government approval, or the like. Likewise, some contracts having particular characteristics, such as, parties, subject matter, locale, terms, value/cost, or the like, may be more likely to result in successful outcomes than some other contracts having different characteristics. For example, a routine service or production contract between two domestic organizations may have less risk than a contract to provide a raw material from a remote area prone to local disruption (e.g., political upheaval, logistical problems, extreme weather events, or the like). Often, organizations may have little insight into how the many characteristics of a complex contract, such as, parties, political conditions, choice of law, venues, forums, geographic locale, subject matter, value/cost, or the like, may impact the process of obtaining an executed contract as well as how contract characteristics impact the likelihood of contract performance. Accordingly, in some cases, it may be difficult for organizations to predict the time or effort it may take to obtain a particular contract. Likewise, it may be difficult for organizations to predict the potential of non-performance for mitigation planning. Thus, it is with respect to these considerations and others that the present invention has been made.